An efficient 1,2,4-triazine-based route to the louisianin alkaloids

Catozzi, Nicola; Wasnaire, Pierre; Taylor, Richard J.K.

doi:10.1016/j.tetlet.2008.03.026

Cited by 21 publications

(10 citation statements)

References 20 publications

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“…In some cases the reaction affords the corresponding 1,2,4‐triazine‐4‐oxides, which can be easily reduced to the target 1,2,4‐triazines. Based on 2‐hydroxyacetophenones a synthetic approach was also proposed: the reaction proceeds via the in situ formation of the corresponding glyoxal derivatives followed by the reaction with amidrazones affording the desired products . However, the serious drawback of this approach is the formation of isomeric 3,5‐disubstituted 1,2,4‐triazines as side‐products.…”

Section: Resultsmentioning

confidence: 99%

“…Based on 2-hydroxyacetophenones a synthetic approach was also proposed: the reaction proceeds via the in situ formation of the corresponding glyoxal derivatives followed by the reaction with amidrazones affording the desired products. [13] However, the serious drawback of this approach is the formation of isomeric 3,5-disubstituted 1,2,4-triazines as side-products. Some other approaches were also reported, such as the thermolysis of a-azido ketone acylhydrazones, [14] the interaction of iso-nitrosoacetophenones either with amidrazones in acidic conditions (in some cases the 1,2,4triazine-4-oxides are also formed [15] ), or with hydrazones of aldehydes.…”

Section: Resultsmentioning

confidence: 99%

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Pot, Atom, Step Economic (PASE) Approach towards (Aza)‐2,2′‐Bipyridines: Synthesis and Photophysical Studies

et al. 2018

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An efficient approach towards α‐unsubstituted‐2,2′‐bipyridines, their aza‐analogs and 3,6‐disubstituted‐1,2,4‐triazine precursors is reported via pot, atom, step economic (PASE) process starting from isonitrosoacetophenone hydrazone and readily available hetero‐arylnitriles. The crystal structures of three key compounds were confirmed by means of X‐ray diffraction analysis. In addition the photophysical properties of the new (aza)‐2,2′‐pyridines were studied.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Pot, Atom, Step Economic (PASE) Approach towards (Aza)‐2,2′‐Bipyridines: Synthesis and Photophysical Studies

et al. 2018

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“…In 2009, Taylor and co-workers took advantage of the 1,2,4-triazine IEDDA reaction to finish the total synthesis of these four alkaloids (Scheme ). , Central to the synthetic route to Louisianin A–D is the [4 + 2] cycloaddition of 1,2,4-triazine 112 with cyclic enamine in situ generated from cyclopentanone and pyrroline. This reaction could be carried out under the microwave condition to provide the desired pyridine 113 in 80% yield.…”

Section: 24-triazinesmentioning

confidence: 99%

Triazines: Syntheses and Inverse Electron-demand Diels–Alder Reactions

et al. 2021

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Triazines are an important class of six-membered aromatic heterocycles possessing three nitrogen atoms, resulting in three types of regio-isomers: 1,2,4-triazines (a-triazines), 1,2,3-triazines (v-triazines), and 1,3,5-triazines (s-triazines). Notably, the application of triazines as cyclic aza-dienes in inverse electron-demand Diels–Alder (IEDDA) cycloaddition reactions has been established as a unique and powerful method in N-heterocycle synthesis, natural product preparation, and bioorthogonal chemistry. In this review, we comprehensively summarize the advances in the construction of these triazines via annulation and ring-expansion reactions, especially emphasizing recent developments and challenges. The synthetic transformations of triazines are focused on IEDDA cycloaddition reactions, which have allowed access to a wide scope of heterocycles, including pyridines, carbolines, azepines, pyridazines, pyrazines, and pyrimidines. The utilization of triazine IEDDA reactions as key steps in natural product synthesis is also discussed. More importantly, a particular attention is paid on the bioorthogonal application of triazines in fast click ligation with various strained alkenes and alkynes, which opens a new opportunity for studying biomolecules in chemical biology.

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“…WK-4028 found in a Louisiana soil sample . Four distinct strategies toward the louisianin alkaloids have appeared, and two syntheses of 39 are reported …”

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confidence: 99%

Synthesis of 2-Pyridones by Cycloreversion of [2.2.2]- Bicycloalkene Diketopiperazines

2014

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A general strategy for the conversion of [2.2.2]-diazabicyclic alkene structures to 2-pyridone aromatic heterocyclic products is reported. The reaction sequence starts from 2,5-diketopiperazine (DKP) derivatives, is compatible with both aromatic and aliphatic aldehyde components, and can intercept either intra- or intermolecular cycloaddition manifolds. Priming of one aza-bridging function in the intermediate [2.2.2]-DKP scaffold permits cycloreversion (microwave heating) and selective extrusion of cyanate derivatives leading to the formation of 2-pyridone structures. Progress toward the synthesis of louisianin A and B, antiproliferative 2-pyridone natural products, is also disclosed.

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An efficient 1,2,4-triazine-based route to the louisianin alkaloids

Cited by 21 publications

References 20 publications

Pot, Atom, Step Economic (PASE) Approach towards (Aza)‐2,2′‐Bipyridines: Synthesis and Photophysical Studies

Pot, Atom, Step Economic (PASE) Approach towards (Aza)‐2,2′‐Bipyridines: Synthesis and Photophysical Studies

Triazines: Syntheses and Inverse Electron-demand Diels–Alder Reactions

Synthesis of 2-Pyridones by Cycloreversion of [2.2.2]- Bicycloalkene Diketopiperazines

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